Trifluoroacetic acid → 2(R)-[2,2-difluoro-1(S)-(4-fluorophenyl)-2-(4-methylsulfanyl-phenoxy)ethylamino]-3-mercaptopropionic acid

HRID 907629Notes

Reaction equation

HRID 907629 reaction equation
[F:1][C:2]([F:46])([O:37][C:38]1[CH:43]=[CH:42][C:41]([S:44][CH3:45])=[CH:40][CH:39]=1)[C@@H:3]([NH:11][C@@H:12]([CH2:16][S:17]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:13]([OH:15])=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[F:46][C:2]([F:1])([O:37][C:38]1[CH:39]=[CH:40][C:41]([S:44][CH3:45])=[CH:42][CH:43]=1)[C@@H:3]([NH:11][C@@H:12]([CH2:16][SH:17])[C:13]([OH:15])=[O:14])[C:4]1[CH:5]=[CH:6][C:7]([F:10])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 673922812(R)-[2,2-difluoro-1(S)-(4-fluorophenyl)-2-(4-methylsulfanylphenoxy)ethylamino]-3-tritylsulfanylpropionic acid

Product 1

HCID 867614002(R)-[2,2-difluoro-1(S)-(4-fluorophenyl)-2-(4-methylsulfanyl-phenoxy)ethylamino]-3-mercaptopropionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2(R)-[2,2-difluoro-1(S)-(4-fluorophenyl)-2-(4-methylsulfanylphenoxy)-ethylamino]-3-tritylsulfanylpropionic acid (0.69 g, 1.04 mmol) in DCM (0.8 ml), TFA (0.322 ml, 4.18 mmol) and triethylsilane (0.332 ml) were added. After stirring 3 h, solvent and excess of TFA were evaporated under vacuum. The residue was dissolved in benzene and evaporated again on rotary evaporator to give 2(R)-[2,2-difluoro-1(S)-(4-fluorophenyl)-2-(4-methylsulfanyl-phenoxy)ethylamino]-3-mercaptopropionic acid. The residue was dissolved in 1N NaOH (4 ml) and the solution was used immediately in the next step.

Workup

  1. customsolvent and excess of TFA were evaporated under vacuum
  2. dissolutionThe residue was dissolved in benzene
  3. customevaporated again on rotary evaporator

Sources & evidence

ORD record
ord-2e5f9c85651543b384c95bb78ff3551d
Source dataset
uspto-grants-2011_09
Patent number
US08013186B2

Reaction notes

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